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As far as despising office work...I sometimes have to agree with you there. My problem is having the time to do it. One option could be to hire a part-time bookeeper/office assistant. It's difficult to train a laborer, but even more difficult to train an office worker. You'd have to decide what their tasks would be beforehand. If you use a program like Quickbooks, you could hire someone to do the tedious data entry for you on a part-time basis.
As far as your leech goes, I'd let him know that reliability is one of the most important aspects of holding down the job. If you can't rely on him...you don't need him. He should still be within a probationary period so you oughta have no problem letting him go. Regardless of whether he'll qualify for unemployment, if he isn't pulling his weight, then he's dead-weight to you.
I've got four guys working for me: my dad (age 58), one 25yr old guy, a 22 yr old, and a new employee who just turned 20. My dad is (of course) reliable and trustworthy, but he can handle a certain pace and that's fine. The 25yr old and 22yr old have been with me several seasons now and are both solid employees, with the older one acting as a foreman for me. The new guy is still in the "deer caught in the headlights" stage. Basically, I think he's in shock as to what actual physical labor is all about. The jury is still out on him. Bottom line, I can teach skills, but I can't teach work ethic. People either have it, or they don't. The best I can do is try to let them find it within themselves. I can read the eyes of the new guy, he's asking whether or not he can hack doing this all summer before heading back to school. He'll either keep pace or he'll be left behind and unemployed, that's the way it goes.
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